Massive parallel catalyst screening: Toward asymmetric MCRs

被引：107

作者：

Kusebauch, U

Beck, B

Messer, K

Herdtweck, E

Domling, A

机构：

[1] Morphochem AG, D-81379 Munich, Germany

[2] Univ Munich, Anorgan Chem Inst Tech, D-85747 Garching, Germany

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 22期

关键词：

D O I：

10.1021/ol035010u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHIC] Hundreds of Lewis acid/ligand combinations have been screened for stereochemical induction in the Passerini multicomponent reaction. The combination of titan tetraisopropylate and (4S,5S)-4,5-bis(diphenylhydroxymethyl)-2,2-dimethyidioxolane was found to give enantiomeric excesses between 32% and 42% in several examples. The absolute stereo induction of one example was determined chemically and by means of X-ray crystallography. This comprises the first asymmetric Passerini reaction and the first example of a stereochernical induction in an isocyanide based multicomponent reaction by a chiral Lewis acid.

引用

页码：4021 / 4024

页数：4

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[1] Short and diverse route toward complex natural product-like macrocycles [J].